methyl (1S,2R,10S,15S,17S,18R,20R)-17-ethyl-3-methyl-20-phenylmethoxy-14-sulfanylidene-15-tri(propan-2-yl)silyloxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate | 910558-52-0

分子结构分类

有机化合物 - 生物碱及其衍生物 - 鸡蛋花型生物碱

中文名称

——

中文别名

——

英文名称

methyl (1S,2R,10S,15S,17S,18R,20R)-17-ethyl-3-methyl-20-phenylmethoxy-14-sulfanylidene-15-tri(propan-2-yl)silyloxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate

英文别名

——

methyl (1S,2R,10S,15S,17S,18R,20R)-17-ethyl-3-methyl-20-phenylmethoxy-14-sulfanylidene-15-tri(propan-2-yl)silyloxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate化学式

CAS

910558-52-0

化学式

C₃₈H₅₂N₂O₅SSi

mdl

——

分子量

676.993

InChiKey

WMCXWFNCOJQCAW-PQTONIMLSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

7.37
重原子数：

47
可旋转键数：

11
环数：

7.0
sp3杂化的碳原子比例：

0.63
拓扑面积：

92.6
氢给体数：

0
氢受体数：

7

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	methyl (1S,2R,10S,17S,18R,20R)-17-ethyl-3-methyl-14-oxo-20-phenylmethoxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate	910558-46-2	C₂₉H₃₂N₂O₅	488.583

下游产品

中文名称	英文名称	CAS号	化学式	分子量
温都罗新	(-)-vindorosine	5231-60-7	C₂₄H₃₀N₂O₅	426.513

反应信息

作为反应物：

描述：

methyl (1S,2R,10S,15S,17S,18R,20R)-17-ethyl-3-methyl-20-phenylmethoxy-14-sulfanylidene-15-tri(propan-2-yl)silyloxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate 在 platinum(IV) oxide 、镍氢气、 sodium acetate 作用下，以四氢呋喃、甲醇、乙酸乙酯为溶剂， 23.0 ℃ 、310.26 kPa 条件下，反应 23.0h，生成 (2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-5-hydroxy-6-methyl-2-triisopropylsilanyloxy-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

参考文献：

名称：

（-）-和ent-（+）-vindorosine的全合成：串联分子内Diels-Alder / 1,3-偶极环加成1,3,4-恶二唑。

摘要：

DOI：

10.1002/anie.200503024
作为产物：

描述：

methyl (1S,2R,10S,17S,18R,20R)-17-ethyl-3-methyl-14-oxo-20-phenylmethoxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate 在劳森试剂、双(三甲基硅基)过氧化物、 lithium diisopropyl amide 作用下，以四氢呋喃、甲苯为溶剂，反应 14.0h，生成 methyl (1S,2R,10S,15S,17S,18R,20R)-17-ethyl-3-methyl-20-phenylmethoxy-14-sulfanylidene-15-tri(propan-2-yl)silyloxy-19-oxa-3,13-diazahexacyclo[15.2.1.02,10.04,9.010,18.013,18]icosa-4,6,8-triene-1-carboxylate

参考文献：

名称：

（-）-和ent-（+）-vindorosine的全合成：串联分子内Diels-Alder / 1,3-偶极环加成1,3,4-恶二唑。

摘要：

DOI：

10.1002/anie.200503024

点击查看最新优质反应信息

文献信息

Total Synthesis of (−)- andent-(+)-Vindorosine: Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition of 1,3,4-Oxadiazoles

作者：Gregory I. Elliott、Juraj Velcicky、Hayato Ishikawa、YongKai Li、Dale L. Boger

DOI：10.1002/anie.200503024

日期：2006.1.16

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